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He moved to New York at the age of 18 to try to become an actor. He graduated from the American Musical and Dramatic Academy's two year program in Manhattan, where, from 1986 to 1989, he worked at the Empire Diner. "I wasn't a great waiter. I was funny, but I gave a lot of attitude", he told Rosie Magazine in March 2002. He added: "The place is like a vortex for me". In 1989, the diner was where he met Tom Fontana (Writer and Director of Oz), who lived around the corner from the diner.[citation needed]

He did some stage work during this time. "I was doing plays all the time, but there's no money in it", Tergesen said in a 1995 Los Angeles Times article, "After graduation, I thought I'd be making a living at it". He went to Los Angeles to help Tom Fontana move house. While dining at a restaurant on the day after arriving in Los Angeles, California, a casting director and friend of Fontana's asked Lee if he was an actor. "He told me there was a part in this movie and at that time, I couldn't imagine what it could be", Tergesen told the L.A. Times. The movie ended up being Point Break, starring Keanu Reeves and Patrick Swayze. "It was the beginning of me never having to do anything else but act", he told LT.com in 1990.

He married Yuko Otomo in 2011; their daughter Lily was born December 5, 2012. He is the brother-in-law of actress Toni Lewis through her marriage to Lee's brother, Chris Tergesen (who served as the music supervisor on Oz).